I feel the episode has been reevaluated and people think because it's funny, it's fine but I agree it sucks. The problem is it is like THE moment when they officially fully prioritized jokes over having actual emotion, meaningful plots or consistent characters
It slso showed a level of meta humor which indicated the show was becoming to self aware for it's own good. This is also clear in Homer's Enemy, which despite geing beloved now was hated by fans when it aired
Still not the jump the shark moment though. That will always be Homer vs Dignity.
The only other Simpsons episode I hate this much is Treehouse of Horror VII, the one with Hugo. I know it’s not canon but I’m not even comfortable with jokes about treating children that way.
Viewed in isolation, the good jokes made it work -- especially in light of the self-awareness typified by photo attached. As an emblem of continuity being for suckers, I don't like it.
The weird thing is, I don't usually like continuity in comic books. I think Marvel should periodic Crises to clean everything out like DC does. But this episode has a smug tone that rubs me the wrong way.
That's what gets me. I don't think authors owe their audiences anything, but antagonizing fans without winning them back over is a good way to lose them!
Really the biggest issue with it is that all of the good "what would Skinner do if he weren't principal?" gags had already been done in much stronger episodes.
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Still not the jump the shark moment though. That will always be Homer vs Dignity.